commonly thought of as meaning trousers that are too short, 'jack-ups' are actually trousers that, surprise surprise, have been 'jacked' up. That means that the waistband has been pulled higher than necessary, possibly up to the naval (bellybutton) or chest.
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It basically means to masturbate, or jack him off
It is a symbol of power and leadership to him
will you jack me off
It seems to mean that Jack's presence was drawing out the evil in Roger.
Jack Glamour Kills. Its his clothing line.